(3aR,8aR)-N,N,2,2-tetramethyl-4,4,8,8-tetraphenyl-hexahydro-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepin-6-amine

• ChemBase ID: 140057
• Molecular Formular: C33H34NO4P
• Molecular Mass: 539.601121
• Monoisotopic Mass: 539.2225452
• SMILES: CC1(O[C@@H]2[C@@H](O1)C(OP(OC2(c1ccccc1)c1ccccc1)N(C)C)(c1ccccc1)c1ccccc1)C
• Canonical SMILES: CN(P1OC(c2ccccc2)(c2ccccc2)[C@H]2[C@H](C(O1)(c1ccccc1)c1ccccc1)OC(O2)(C)C)C
• InChI: InChI=1S/C33H34NO4P/c1-31(2)35-29-30(36-31)33(27-21-13-7-14-22-27,28-23-15-8-16-24-28)38-39(34(3)4)37-32(29,25-17-9-5-10-18-25)26-19-11-6-12-20-26/h5-24,29-30H,1-4H3/t29-,30-/m1/s1
• InChIKey: DRPNADVMTMEWQY-LOYHVIPDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3aR,8aR)-N,N,2,2-tetramethyl-4,4,8,8-tetraphenyl-hexahydro-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepin-6-amine
• IUPAC Traditional name: (3aR,8aR)-N,N,2,2-tetramethyl-4,4,8,8-tetraphenyl-dihydro-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepin-6-amine
• Synonyms: (3aR,8aR)-(-)-(2,2-Dimethyl-4,4,8,8-tetraphenyl-tetrahydro-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepin-6-yl)dimethylamine; (3aR,8aR)-(-)-(2,2-二甲基-4,4,8,8-四苯基-四氢-[1,3]二噁唑并[4,5-e][1,3,2]二噁磷杂庚英-6-基)二甲基胺

Database IDs

• CAS Number: 213843-90-4
• MDL Number: MFCD04117685
• PubChem SID: 24884738; 162234301
• PubChem CID: 11145951

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 5.9198694
• LogD (pH = 7.4): 7.4603376
• Log P: 7.7171
• Molar Refractivity: 154.9582 cm^3
• Polarizability: 61.23678 Å^3
• Polar Surface Area: 40.16 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 218-221 °C

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 96%
• Empirical Formula (Hill Notation): C33H34NO4P

DETAILS

Sigma Aldrich - 665460

Application
Phosphoramidite ligand employed in an asymmetric, iridium-catalyzed, allylic allylation of propenylboronates.1 Also used in a copper-catalyzed asymmetric conjugate addition of diethylzinc to α,β-unsaturated imines derived from amino acids.2
DSM MonoPhos Family of Highly Efficient Privileged Ligands
Packaging
100, 500 mg in glass bottle
Legal Information
Sold under license from DSM for research purposes only.